Poly[piperazinediium [[aqua­bismuth­ate(III)]-di-μ-pyridine-2,6-dicarboxyl­ato-bis­muthate(III)-di-μ-pyridine-2,6-dicarboxyl­ato] monohydrate]

Aghabozorg, H.; Nemati, A.; Derikvand, Z.; Ghadermazi, M.

doi:10.1107/S160053680800161X

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page m374

doi:10.1107/S160053680800161X

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Poly[piperazinediium [[aquabismuthate(III)]-di-μ-pyridine-2,6-dicarboxylato-bismuthate(III)-di-μ-pyridine-2,6-dicarboxylato] monohydrate]

Hossein Aghabozorg,^a ^* Andya Nemati,^a Zohreh Derikvand ^a and Mohammad Ghadermazi ^b

^aFaculty of Chemistry, Teacher Training University, 49 Mofateh Avenue, 15614 Tehran, Iran, and ^bDepartment of Chemistry, University of Kurdistan, Sanandaj, Iran
^*Correspondence e-mail: haghabozorg@yahoo.com

(Received 5 November 2007; accepted 15 January 2008; online 23 January 2008)

The title compound, {(C₄H₁₂N₂)[Bi₂(C₇H₃NO₄)₄(H₂O)]·H₂O}_n or {(pipzH₂)[Bi₂(pydc)₄(H₂O)]·H₂O}_n, where pydcH₂ is pyridine-2,6-dicarboxylic acid and pipz is piperazine, was obtained by reaction of Bi(NO₃)₃·5H₂O with (pipzH₂)(pydcH)₂·3H₂O in a 1:2 molar ratio in aqueous solution. There are two independent Bi^III atoms in the structure, one of which is eight-coordinate with a distorted bicapped trigonal-prismatic geometry, and another which is nine-coordinate with a distorted tricapped trigonal-prismatic geometry. The carboxylate groups of the (pydc)²⁻ ligands link dinuclear [Bi₂(C₇H₃NO₄)₄(H₂O)]²⁻ units into one-dimensional coordination polymers. The pipzH₂²⁺ cations (site symmetry $[\overline{1}]$ ) and non-coordinated water molecules lie between these polymers, forming N—H⋯O and O—H⋯O hydrogen bonds to the O atoms of the carboxylate groups.

Related literature

For related literature, see: Aghabozorg, Attar Gharamaleki, Ghadermazi et al. (2007 ); Aghabozorg, Attar Gharamaleki, Ghasemikhah et al. (2007 ); Aghabozorg, Motyeian et al. (2007 ); Aghabozorg, Daneshvar et al. (2007 ); Sharif et al. (2007 ); Sheshmani et al. (2006 ).

Experimental

Crystal data

(C₄H₁₂N₂)[Bi₂(C₇H₃NO₄)₄(H₂O)]·H₂O
M_r = 1202.56
Triclinic, $[P \overline 1]$
a = 10.8111 (4) Å
b = 12.1660 (5) Å
c = 14.0402 (5) Å
α = 96.094 (1)°
β = 93.169 (1)°
γ = 113.848 (1)°
V = 1669.65 (11) Å³
Z = 2
Mo Kα radiation
μ = 10.62 mm⁻¹
T = 100 (2) K
0.15 × 0.15 × 0.10 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.204, T_max = 0.346
22723 measured reflections
8005 independent reflections
6952 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.022
wR(F²) = 0.048
S = 1.03
8005 reflections
523 parameters
H-atom parameters constrained
Δρ_max = 1.32 e Å⁻³
Δρ_min = −0.82 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H5N1⋯O2Wⁱ	0.90	2.00	2.761 (4)	141
N5—H5N2⋯O6	0.90	1.86	2.722 (4)	160
N6—H6N1⋯O16ⁱⁱ	0.90	1.78	2.676 (4)	176
N6—H6N2⋯O12	0.90	1.95	2.762 (4)	149
O1W—H1W1⋯O7	0.85	2.08	2.891 (3)	160
O1W—H1W2⋯O9ⁱⁱⁱ	0.85	2.53	3.337 (4)	158
O2W—H2W1⋯O14	0.85	2.04	2.887 (4)	176
O2W—H2W2⋯O5	0.85	2.35	3.162 (4)	159
Symmetry codes: (i) -x, -y+2, -z+1; (ii) -x-1, -y, -z; (iii) -x, -y+1, -z.

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680800161X/bi2264sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680800161X/bi2264Isup2.hkl

checkCIF report

Comment top

The preparation and characterization of self-assembling systems have been considered by chemists in recent years. A literature review shows that the (pydc)^2- ligand can form complexes with transition metals (Aghabozorg, Attar Gharamaleki, Ghadermazi et al., 2007; Aghabozorg, Attar Gharamaleki, Ghasemikhah et al., 2007; Aghabozorg, Motyeian et al., 2007; Aghabozorg, Daneshvar et al., 2007; Sharif et al., 2007). In this work, (pydc)^2- acts as tridentate ligand with one N atom of pyridine and two O atoms of carboxylates acting as donors and also has a bridging role between the binuclear units containing Bi1 and Bi2. The binuclear units consist of two Bi^III atoms, four (pydc)^2- ligands, and one coordinated water molecule, while one (pipzH₂)²⁺ cation and one uncoordinated water molecule are also present in the asymmetric unit (Fig. 1).

Two Bi1—O7—C14—O8—Bi2 bridging bonds between neighboring binuclear units link them together and form several rings with four Bi^III atoms, six O atoms and two C atoms (Fig. 2). Atom Bi1 is eight coordinated by two tridentate (pydc)^2- ligands, one O atom from the Bi1—O9—Bi2 bridge and one O atom from the neighbouring carboxylate group (Bi1—O14ⁱ = 2.971 (3) Å, symmetry code: (i) -x, 1 - y, 1 - z). Atom Bi2 is nine coordinated by two tridentate (pydc)^2- ligands, one O atom from the Bi1—O1—Bi2 bridge, one O atom from a coordinated water molecule (Bi2—O1W = 2.960 (3) Å) and one O atom from a neighbouring carboxylate group (Bi2—O8ⁱⁱ = 2.883 (2) Å, symmetry code: (ii) -x, 1 - y, -z). The sum of the van der Waals radii for Bi and O is 3.86 Å, which is significantly longer than the bond distances for Bi1—O14ⁱ and Bi2—O8ⁱⁱ. The coordination polyhedron around Bi1 is a distorted bicapped trigonal prism which is nearly eclipsed, in which O1, O7, O9 and O3, O5, O14 form two triangles and N1 and N2 form two caps of the prism. The sum of the bond angles N3—Bi2—O1W (113.37 (8)°), O1W—Bi2—N4 (125.24 (8)°) and N4—Bi2—N3 (121.00 (9)°) is equal to 359.61°, indicating that Bi2 is located in the center of the O1W/N3/N4 plane. Atoms O8, O11, O15 and O1, O9, O13 build two triangles. So, a prism consisting of six O atoms and three caps (N3, N4 and O1W) on its faces is formed around Bi2, that is the coordination polyhedron may be described as a distorted tricapped trigonal prism.

N—H···O hydrogen bonds are formed between (pipzH₂)²⁺ and the carboxylate groups (Table1) and also O—H···O hydrogen bonds are formed between uncoordinated water molecules and the carboxylate groups. In addition, C—H···O contacts with C···O distances ranging from 2.887 (4)Å to 3.656 (4) Å are observed between (pipzH₂)²⁺ cations and carboxylate groups. There are C29—H29B···Cg1 interactions (3.638 (5) Å; x, y + 1, z), where Cg1 is the centroid of the N4/C23—C27 ring and also C32—H32B···Cg2 interactions (3.656 (5) Å; x - 1,y, z), where Cg2 is the centroid of the N2/C9—C13 ring (Fig. 3).

Related literature top

For related literature, see: Aghabozorg, Attar Gharamaleki, Ghadermazi et al. (2007); Aghabozorg, Attar Gharamaleki, Ghasemikhah et al. (2007); Aghabozorg, Motyeian et al. (2007); Aghabozorg, Daneshvar et al. (2007); Sharif et al. (2007); Sheshmani et al. (2006).

Experimental top

The proton transfer compound (pipzH₂)(pydcH)₂.3H₂O was prepared by reaction of pyridine-2,6-dicarboxylic acid (pydcH₂) with piperazine (pipz) (Sheshmani et al., 2006). A solution of Bi(NO₃)₃.5H₂O (242 mg, 0.5 mmol) in water (25 ml) was added to (pipzH₂)(pydcH)₂.3H₂O (253 mg, 1.0 mmol) in 25 ml water and colorless crystals were obtained by slow evaporation of the solvent at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: APEX2 (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit of the title compound with displacement ellipsoids drawn at 50% probability for non-H atoms.
	Fig. 2. Rings of four Bi^III atoms within the 1-D coordination polymers.
	Fig. 3. Crystal packing with hydrogen bonds shown as dashed lines.

Poly[piperazinediium [[aquabismuthate(III)]-di-µ-pyridine-2,6-dicarboxylato- bismuthate(III)-di-µ-pyridine-2,6-dicarboxylato] monohydrate] top

Crystal data top

(C₄H₁₂N₂)[Bi₂(C₇H₃NO₄)₄(H₂O)]·H₂O	Z = 2
M_r = 1202.56	F(000) = 1144
Triclinic, P1	D_x = 2.392 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.8111 (4) Å	Cell parameters from 5207 reflections
b = 12.1660 (5) Å	θ = 2.6–29.4°
c = 14.0402 (5) Å	µ = 10.62 mm⁻¹
α = 96.094 (1)°	T = 100 K
β = 93.169 (1)°	Prism, colourless
γ = 113.848 (1)°	0.15 × 0.15 × 0.10 mm
V = 1669.65 (11) Å³

Data collection top

Bruker SMART APEXII CCD diffractometer	8005 independent reflections
Radiation source: fine-focus sealed tube	6952 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
ϕ and ω scans	θ_max = 28.0°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −14→14
T_min = 0.204, T_max = 0.346	k = −16→16
22723 measured reflections	l = −18→18

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.022	Hydrogen site location: difference Fourier map
wR(F²) = 0.048	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.019P)²] where P = (F_o² + 2F_c²)/3
8005 reflections	(Δ/σ)_max = 0.001
523 parameters	Δρ_max = 1.32 e Å⁻³
0 restraints	Δρ_min = −0.82 e Å⁻³

Crystal data top

(C₄H₁₂N₂)[Bi₂(C₇H₃NO₄)₄(H₂O)]·H₂O	γ = 113.848 (1)°
M_r = 1202.56	V = 1669.65 (11) Å³
Triclinic, P1	Z = 2
a = 10.8111 (4) Å	Mo Kα radiation
b = 12.1660 (5) Å	µ = 10.62 mm⁻¹
c = 14.0402 (5) Å	T = 100 K
α = 96.094 (1)°	0.15 × 0.15 × 0.10 mm
β = 93.169 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	8005 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	6952 reflections with I > 2σ(I)
T_min = 0.204, T_max = 0.346	R_int = 0.031
22723 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.022	0 restraints
wR(F²) = 0.048	H-atom parameters constrained
S = 1.03	Δρ_max = 1.32 e Å⁻³
8005 reflections	Δρ_min = −0.82 e Å⁻³
523 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Bi1	0.187854 (12)	0.622892 (10)	0.307230 (9)	0.01470 (4)
Bi2	−0.184337 (12)	0.356548 (10)	0.178059 (9)	0.01477 (4)
O1	0.0427 (2)	0.3934 (2)	0.26028 (18)	0.0193 (5)
O2	0.0375 (3)	0.2059 (2)	0.23943 (18)	0.0225 (5)
O3	0.4159 (2)	0.7303 (2)	0.35552 (17)	0.0195 (5)
O4	0.6152 (3)	0.7375 (2)	0.41582 (19)	0.0246 (6)
O5	0.1821 (3)	0.8179 (2)	0.39201 (17)	0.0202 (5)
O6	0.2563 (3)	1.0190 (2)	0.39225 (18)	0.0228 (5)
O7	0.2296 (2)	0.5669 (2)	0.15750 (17)	0.0175 (5)
O8	0.2740 (3)	0.6124 (2)	0.01038 (17)	0.0207 (5)
O9	−0.0239 (2)	0.5885 (2)	0.20041 (18)	0.0196 (5)
O10	−0.0098 (2)	0.7798 (2)	0.21948 (19)	0.0225 (5)
O11	−0.4218 (2)	0.2606 (2)	0.15982 (18)	0.0203 (5)
O12	−0.6215 (2)	0.2613 (2)	0.11226 (19)	0.0234 (5)
O13	−0.1855 (3)	0.4370 (2)	0.33567 (17)	0.0193 (5)
O14	−0.2198 (3)	0.4114 (2)	0.48793 (18)	0.0228 (5)
O15	−0.2214 (2)	0.1481 (2)	0.10123 (17)	0.0183 (5)
O16	−0.2602 (3)	−0.0419 (2)	0.12412 (18)	0.0226 (5)
N1	0.3057 (3)	0.4903 (3)	0.3281 (2)	0.0165 (6)
N2	0.2716 (3)	0.7927 (2)	0.2211 (2)	0.0152 (6)
N3	−0.2965 (3)	0.4993 (2)	0.1700 (2)	0.0161 (6)
N4	−0.2525 (3)	0.2036 (2)	0.2842 (2)	0.0164 (6)
C1	0.0944 (4)	0.3157 (3)	0.2662 (2)	0.0180 (7)
C2	0.2423 (4)	0.3687 (3)	0.3098 (2)	0.0171 (7)
C3	0.3090 (4)	0.2964 (3)	0.3301 (2)	0.0191 (7)
H3A	0.2627	0.2105	0.3175	0.023*
C4	0.4432 (4)	0.3505 (3)	0.3688 (3)	0.0221 (7)
H4A	0.4899	0.3021	0.3841	0.026*
C5	0.5101 (4)	0.4771 (3)	0.3854 (3)	0.0204 (7)
H5A	0.6033	0.5165	0.4104	0.025*
C6	0.4356 (3)	0.5435 (3)	0.3640 (2)	0.0173 (7)
C7	0.4970 (3)	0.6814 (3)	0.3806 (2)	0.0174 (7)
C8	0.2402 (3)	0.9155 (3)	0.3569 (3)	0.0183 (7)
C9	0.2945 (3)	0.9050 (3)	0.2603 (2)	0.0160 (7)
C10	0.3618 (3)	1.0040 (3)	0.2131 (3)	0.0186 (7)
H10A	0.3786	1.0838	0.2414	0.022*
C11	0.4038 (4)	0.9842 (3)	0.1244 (3)	0.0213 (7)
H11A	0.4521	1.0509	0.0918	0.026*
C12	0.3756 (3)	0.8668 (3)	0.0827 (3)	0.0184 (7)
H12A	0.4016	0.8513	0.0209	0.022*
C13	0.3087 (3)	0.7735 (3)	0.1339 (2)	0.0169 (7)
C14	0.2686 (3)	0.6421 (3)	0.0956 (2)	0.0164 (7)
C15	−0.0753 (4)	0.6690 (3)	0.2024 (2)	0.0181 (7)
C16	−0.2269 (3)	0.6196 (3)	0.1788 (2)	0.0167 (7)
C17	−0.2899 (4)	0.6960 (3)	0.1640 (3)	0.0200 (7)
H17A	−0.2392	0.7816	0.1732	0.024*
C18	−0.4288 (4)	0.6453 (3)	0.1355 (3)	0.0213 (7)
H18A	−0.4743	0.6955	0.1229	0.026*
C19	−0.5008 (4)	0.5192 (3)	0.1255 (3)	0.0216 (7)
H19A	−0.5959	0.4819	0.1062	0.026*
C20	−0.4299 (3)	0.4504 (3)	0.1445 (2)	0.0173 (7)
C21	−0.4988 (3)	0.3139 (3)	0.1373 (2)	0.0169 (7)
C22	−0.2236 (3)	0.3715 (3)	0.4019 (3)	0.0181 (7)
C23	−0.2778 (3)	0.2360 (3)	0.3722 (2)	0.0169 (7)
C24	−0.3469 (3)	0.1508 (3)	0.4298 (2)	0.0182 (7)
H24A	−0.3693	0.1749	0.4907	0.022*
C25	−0.3832 (3)	0.0283 (3)	0.3965 (3)	0.0191 (7)
H25A	−0.4301	−0.0325	0.4348	0.023*
C26	−0.3498 (3)	−0.0034 (3)	0.3066 (3)	0.0183 (7)
H26A	−0.3702	−0.0858	0.2834	0.022*
C27	−0.2863 (3)	0.0871 (3)	0.2518 (2)	0.0167 (7)
C28	−0.2530 (3)	0.0622 (3)	0.1510 (3)	0.0184 (7)
N5	0.1037 (3)	1.1154 (3)	0.4887 (2)	0.0199 (6)
H5N1	0.1350	1.1969	0.4971	0.024*
H5N2	0.1704	1.0994	0.4636	0.024*
C29	−0.0256 (4)	1.0593 (3)	0.4221 (3)	0.0216 (7)
H29A	−0.0078	1.0848	0.3577	0.026*
H29B	−0.0931	1.0876	0.4471	0.026*
C30	0.0819 (4)	1.0776 (3)	0.5865 (3)	0.0210 (7)
H30A	0.0173	1.1065	0.6159	0.025*
H30B	0.1692	1.1143	0.6286	0.025*
N6	−0.8584 (3)	0.0656 (3)	0.0345 (2)	0.0192 (6)
H6N1	−0.8147	0.0590	−0.0171	0.023*
H6N2	−0.7844	0.1111	0.0761	0.023*
C31	−0.9440 (4)	0.1308 (3)	0.0061 (3)	0.0216 (7)
H31A	−0.8868	0.2061	−0.0189	0.026*
H31B	−0.9830	0.1534	0.0632	0.026*
C32	−0.9431 (4)	−0.0495 (3)	0.0703 (3)	0.0231 (8)
H32A	−0.9823	−0.0312	0.1287	0.028*
H32B	−0.8854	−0.0917	0.0878	0.028*
O1W	0.0082 (3)	0.3774 (2)	0.0319 (2)	0.0287 (6)
H1W1	0.0826	0.4211	0.0666	0.043*
H1W2	0.0135	0.4062	−0.0211	0.043*
O2W	−0.0696 (3)	0.6708 (2)	0.5000 (2)	0.0348 (7)
H2W1	−0.1177	0.5951	0.4969	0.052*
H2W2	−0.0142	0.6958	0.4583	0.052*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Bi1	0.01464 (7)	0.01425 (6)	0.01526 (7)	0.00582 (5)	0.00170 (5)	0.00288 (5)
Bi2	0.01454 (7)	0.01311 (6)	0.01629 (7)	0.00520 (5)	0.00116 (5)	0.00279 (5)
O1	0.0178 (12)	0.0164 (11)	0.0229 (13)	0.0061 (10)	0.0002 (10)	0.0041 (10)
O2	0.0236 (14)	0.0161 (11)	0.0245 (13)	0.0058 (10)	−0.0020 (11)	0.0011 (10)
O3	0.0184 (12)	0.0182 (11)	0.0207 (13)	0.0064 (10)	0.0001 (10)	0.0037 (10)
O4	0.0189 (13)	0.0227 (13)	0.0304 (15)	0.0072 (11)	−0.0034 (11)	0.0043 (11)
O5	0.0240 (13)	0.0219 (12)	0.0168 (12)	0.0112 (11)	0.0038 (10)	0.0043 (10)
O6	0.0265 (14)	0.0198 (12)	0.0238 (13)	0.0114 (11)	0.0052 (11)	0.0010 (10)
O7	0.0166 (12)	0.0164 (11)	0.0193 (12)	0.0065 (10)	0.0015 (10)	0.0035 (9)
O8	0.0232 (13)	0.0215 (12)	0.0180 (12)	0.0102 (11)	0.0017 (10)	0.0016 (10)
O9	0.0154 (12)	0.0173 (11)	0.0265 (13)	0.0069 (10)	0.0014 (10)	0.0049 (10)
O10	0.0180 (13)	0.0172 (12)	0.0287 (14)	0.0043 (10)	−0.0010 (11)	0.0033 (10)
O11	0.0161 (12)	0.0177 (11)	0.0258 (13)	0.0053 (10)	0.0019 (10)	0.0048 (10)
O12	0.0181 (13)	0.0197 (12)	0.0299 (14)	0.0052 (10)	−0.0018 (11)	0.0051 (10)
O13	0.0245 (13)	0.0161 (11)	0.0178 (12)	0.0091 (10)	−0.0005 (10)	0.0025 (9)
O14	0.0295 (14)	0.0201 (12)	0.0177 (13)	0.0100 (11)	0.0021 (11)	0.0000 (10)
O15	0.0207 (13)	0.0157 (11)	0.0182 (12)	0.0074 (10)	0.0007 (10)	0.0027 (9)
O16	0.0294 (14)	0.0185 (12)	0.0233 (13)	0.0122 (11)	0.0086 (11)	0.0048 (10)
N1	0.0167 (14)	0.0187 (13)	0.0154 (14)	0.0078 (12)	0.0025 (11)	0.0057 (11)
N2	0.0144 (14)	0.0173 (13)	0.0147 (14)	0.0077 (11)	−0.0016 (11)	0.0020 (11)
N3	0.0174 (14)	0.0177 (13)	0.0143 (14)	0.0079 (11)	0.0020 (11)	0.0032 (11)
N4	0.0157 (14)	0.0158 (13)	0.0181 (14)	0.0074 (11)	0.0000 (11)	0.0014 (11)
C1	0.0195 (18)	0.0192 (16)	0.0161 (17)	0.0080 (14)	0.0023 (14)	0.0050 (13)
C2	0.0215 (18)	0.0185 (16)	0.0123 (15)	0.0089 (14)	0.0039 (13)	0.0030 (12)
C3	0.0212 (18)	0.0184 (16)	0.0193 (17)	0.0092 (14)	0.0047 (14)	0.0034 (13)
C4	0.0236 (19)	0.0238 (17)	0.0235 (19)	0.0145 (15)	0.0005 (15)	0.0049 (14)
C5	0.0173 (17)	0.0251 (17)	0.0204 (18)	0.0100 (14)	0.0018 (14)	0.0042 (14)
C6	0.0185 (17)	0.0208 (16)	0.0136 (16)	0.0090 (14)	0.0022 (13)	0.0040 (13)
C7	0.0188 (17)	0.0200 (16)	0.0135 (16)	0.0078 (14)	0.0013 (13)	0.0034 (13)
C8	0.0159 (17)	0.0205 (16)	0.0200 (17)	0.0092 (14)	−0.0008 (14)	0.0031 (14)
C9	0.0149 (16)	0.0167 (15)	0.0175 (17)	0.0076 (13)	−0.0004 (13)	0.0029 (13)
C10	0.0162 (17)	0.0150 (15)	0.0240 (18)	0.0069 (13)	−0.0034 (14)	0.0014 (13)
C11	0.0173 (17)	0.0181 (16)	0.0267 (19)	0.0050 (14)	0.0015 (15)	0.0054 (14)
C12	0.0182 (17)	0.0208 (16)	0.0182 (17)	0.0095 (14)	0.0028 (14)	0.0050 (13)
C13	0.0143 (16)	0.0173 (15)	0.0187 (17)	0.0061 (13)	0.0007 (13)	0.0029 (13)
C14	0.0107 (15)	0.0185 (15)	0.0203 (17)	0.0065 (13)	0.0005 (13)	0.0020 (13)
C15	0.0188 (18)	0.0201 (16)	0.0178 (17)	0.0095 (14)	0.0026 (14)	0.0058 (13)
C16	0.0182 (17)	0.0163 (15)	0.0140 (16)	0.0054 (13)	0.0025 (13)	0.0028 (12)
C17	0.0189 (17)	0.0171 (16)	0.0244 (18)	0.0077 (14)	0.0031 (14)	0.0031 (14)
C18	0.0211 (18)	0.0194 (16)	0.0275 (19)	0.0126 (14)	0.0022 (15)	0.0027 (14)
C19	0.0163 (17)	0.0231 (17)	0.0237 (18)	0.0067 (14)	0.0018 (14)	0.0027 (14)
C20	0.0186 (17)	0.0165 (15)	0.0162 (16)	0.0071 (14)	0.0023 (13)	0.0006 (13)
C21	0.0179 (17)	0.0171 (15)	0.0154 (16)	0.0068 (13)	0.0027 (13)	0.0028 (13)
C22	0.0164 (17)	0.0182 (16)	0.0201 (17)	0.0076 (13)	0.0009 (13)	0.0023 (13)
C23	0.0146 (16)	0.0191 (16)	0.0171 (17)	0.0076 (13)	−0.0007 (13)	0.0015 (13)
C24	0.0152 (16)	0.0231 (17)	0.0150 (16)	0.0071 (14)	0.0000 (13)	0.0009 (13)
C25	0.0171 (17)	0.0194 (16)	0.0203 (18)	0.0059 (14)	0.0021 (14)	0.0074 (13)
C26	0.0175 (17)	0.0161 (15)	0.0203 (17)	0.0064 (13)	−0.0003 (14)	0.0029 (13)
C27	0.0153 (16)	0.0145 (15)	0.0199 (17)	0.0063 (13)	−0.0021 (13)	0.0015 (13)
C28	0.0140 (16)	0.0170 (15)	0.0237 (18)	0.0065 (13)	−0.0017 (14)	0.0024 (13)
N5	0.0190 (15)	0.0161 (13)	0.0242 (16)	0.0061 (12)	0.0037 (12)	0.0046 (12)
C29	0.0200 (18)	0.0232 (17)	0.0218 (18)	0.0087 (15)	0.0016 (14)	0.0054 (14)
C30	0.0167 (17)	0.0198 (16)	0.0216 (18)	0.0039 (14)	−0.0002 (14)	−0.0009 (14)
N6	0.0178 (15)	0.0197 (14)	0.0181 (15)	0.0060 (12)	0.0002 (12)	0.0025 (11)
C31	0.0225 (18)	0.0157 (16)	0.0247 (19)	0.0063 (14)	0.0034 (15)	0.0015 (14)
C32	0.0187 (18)	0.0221 (17)	0.0271 (19)	0.0059 (14)	0.0016 (15)	0.0079 (15)
O1W	0.0237 (14)	0.0264 (14)	0.0319 (15)	0.0067 (11)	0.0002 (12)	0.0035 (12)
O2W	0.0361 (17)	0.0240 (14)	0.0426 (18)	0.0106 (13)	0.0117 (14)	0.0016 (12)

Geometric parameters (Å, º) top

Bi1—O7	2.266 (2)	C8—C9	1.521 (5)
Bi1—O3	2.295 (2)	C9—C10	1.390 (5)
Bi1—N2	2.385 (3)	C10—C11	1.379 (5)
Bi1—N1	2.456 (3)	C10—H10A	0.950
Bi1—O9	2.526 (2)	C11—C12	1.388 (5)
Bi1—O5	2.565 (2)	C11—H11A	0.950
Bi1—O1	2.578 (2)	C12—C13	1.376 (5)
Bi1—O14ⁱ	2.971 (3)	C12—H12A	0.950
Bi2—O13	2.326 (2)	C13—C14	1.505 (4)
Bi2—O11	2.337 (2)	C15—C16	1.503 (5)
Bi2—N4	2.414 (3)	C16—C17	1.382 (5)
Bi2—N3	2.496 (3)	C17—C18	1.388 (5)
Bi2—O1	2.499 (2)	C17—H17A	0.950
Bi2—O15	2.512 (2)	C18—C19	1.398 (5)
Bi2—O9	2.620 (2)	C18—H18A	0.950
Bi2—O8ⁱⁱ	2.883 (2)	C19—C20	1.379 (5)
Bi2—O1W	2.960 (3)	C19—H19A	0.950
O1—C1	1.285 (4)	C20—C21	1.510 (5)
O2—C1	1.227 (4)	C22—C23	1.511 (5)
O3—C7	1.295 (4)	C23—C24	1.380 (5)
O4—C7	1.223 (4)	C24—C25	1.397 (5)
O5—C8	1.266 (4)	C24—H24A	0.950
O6—C8	1.242 (4)	C25—C26	1.391 (5)
O7—C14	1.292 (4)	C25—H25A	0.950
O8—C14	1.224 (4)	C26—C27	1.380 (5)
O8—Bi2ⁱⁱ	2.883 (2)	C26—H26A	0.950
O9—C15	1.306 (4)	C27—C28	1.509 (5)
O10—C15	1.231 (4)	N5—C30	1.496 (5)
O11—C21	1.290 (4)	N5—C29	1.497 (4)
O12—C21	1.228 (4)	N5—H5N1	0.900
O13—C22	1.267 (4)	N5—H5N2	0.900
O14—C22	1.244 (4)	C29—C30ⁱⁱⁱ	1.513 (5)
O14—Bi1ⁱ	2.971 (3)	C29—H29A	0.990
O15—C28	1.260 (4)	C29—H29B	0.990
O16—C28	1.252 (4)	C30—C29ⁱⁱⁱ	1.513 (5)
N1—C6	1.328 (4)	C30—H30A	0.990
N1—C2	1.343 (4)	C30—H30B	0.990
N2—C13	1.336 (4)	N6—C32	1.488 (4)
N2—C9	1.336 (4)	N6—C31	1.505 (4)
N3—C20	1.328 (4)	N6—H6N1	0.900
N3—C16	1.335 (4)	N6—H6N2	0.900
N4—C27	1.333 (4)	C31—C32^iv	1.507 (5)
N4—C23	1.333 (4)	C31—H31A	0.990
C1—C2	1.523 (5)	C31—H31B	0.990
C2—C3	1.384 (5)	C32—C31^iv	1.507 (5)
C3—C4	1.378 (5)	C32—H32A	0.990
C3—H3A	0.950	C32—H32B	0.990
C4—C5	1.397 (5)	O1W—H1W1	0.850
C4—H4A	0.950	O1W—H1W2	0.850
C5—C6	1.394 (5)	O2W—H2W1	0.850
C5—H5A	0.950	O2W—H2W2	0.850
C6—C7	1.520 (5)

O7—Bi1—O3	91.67 (8)	C5—C6—C7	122.4 (3)
O7—Bi1—N2	69.13 (9)	O4—C7—O3	125.1 (3)
O3—Bi1—N2	71.64 (9)	O4—C7—C6	119.6 (3)
O7—Bi1—N1	74.33 (9)	O3—C7—C6	115.3 (3)
O3—Bi1—N1	67.54 (9)	O6—C8—O5	127.0 (3)
N2—Bi1—N1	123.21 (9)	O6—C8—C9	116.3 (3)
O7—Bi1—O9	75.63 (8)	O5—C8—C9	116.7 (3)
O3—Bi1—O9	150.67 (8)	N2—C9—C10	120.8 (3)
N2—Bi1—O9	79.11 (8)	N2—C9—C8	115.7 (3)
N1—Bi1—O9	130.88 (8)	C10—C9—C8	123.5 (3)
O7—Bi1—O5	133.72 (8)	C11—C10—C9	118.9 (3)
O3—Bi1—O5	80.95 (8)	C11—C10—H10A	120.6
N2—Bi1—O5	65.17 (8)	C9—C10—H10A	120.6
N1—Bi1—O5	139.27 (8)	C10—C11—C12	120.0 (3)
O9—Bi1—O5	88.88 (8)	C10—C11—H11A	120.0
O7—Bi1—O1	71.85 (8)	C12—C11—H11A	120.0
O3—Bi1—O1	131.37 (8)	C13—C12—C11	117.7 (3)
N2—Bi1—O1	134.97 (8)	C13—C12—H12A	121.1
N1—Bi1—O1	64.02 (8)	C11—C12—H12A	121.1
O9—Bi1—O1	70.14 (8)	N2—C13—C12	122.4 (3)
O5—Bi1—O1	142.67 (8)	N2—C13—C14	114.6 (3)
O7—Bi1—O14ⁱ	142.66 (8)	C12—C13—C14	122.9 (3)
O3—Bi1—O14ⁱ	75.43 (8)	O8—C14—O7	124.1 (3)
N2—Bi1—O14ⁱ	134.51 (8)	O8—C14—C13	120.0 (3)
N1—Bi1—O14ⁱ	68.34 (8)	O7—C14—C13	115.8 (3)
O9—Bi1—O14ⁱ	129.79 (8)	O10—C15—O9	125.5 (3)
O5—Bi1—O14ⁱ	79.51 (7)	O10—C15—C16	118.7 (3)
O1—Bi1—O14ⁱ	90.47 (7)	O9—C15—C16	115.8 (3)
O13—Bi2—O11	90.55 (9)	N3—C16—C17	121.9 (3)
O13—Bi2—N4	67.58 (9)	N3—C16—C15	117.2 (3)
O11—Bi2—N4	72.05 (9)	C17—C16—C15	120.8 (3)
O13—Bi2—N3	72.91 (9)	C16—C17—C18	118.6 (3)
O11—Bi2—N3	66.29 (9)	C16—C17—H17A	120.7
N4—Bi2—N3	121.00 (9)	C18—C17—H17A	120.7
O13—Bi2—O1	75.37 (8)	C17—C18—C19	119.1 (3)
O11—Bi2—O1	151.73 (8)	C17—C18—H18A	120.5
N4—Bi2—O1	79.89 (9)	C19—C18—H18A	120.5
N3—Bi2—O1	129.27 (8)	C20—C19—C18	118.1 (3)
O13—Bi2—O15	132.74 (8)	C20—C19—H19A	120.9
O11—Bi2—O15	79.38 (8)	C18—C19—H19A	120.9
N4—Bi2—O15	65.37 (8)	N3—C20—C19	122.5 (3)
N3—Bi2—O15	138.11 (8)	N3—C20—C21	115.3 (3)
O1—Bi2—O15	92.19 (7)	C19—C20—C21	122.1 (3)
O13—Bi2—O9	72.26 (8)	O12—C21—O11	124.5 (3)
O11—Bi2—O9	129.51 (8)	O12—C21—C20	119.4 (3)
N4—Bi2—O9	134.46 (8)	O11—C21—C20	116.1 (3)
N3—Bi2—O9	63.32 (8)	O14—C22—O13	124.5 (3)
O1—Bi2—O9	69.86 (8)	O14—C22—C23	119.0 (3)
O15—Bi2—O9	145.72 (8)	O13—C22—C23	116.4 (3)
O13—Bi2—O8ⁱⁱ	135.52 (7)	N4—C23—C24	121.6 (3)
O11—Bi2—O8ⁱⁱ	73.14 (8)	N4—C23—C22	114.2 (3)
N4—Bi2—O8ⁱⁱ	137.85 (8)	C24—C23—C22	124.1 (3)
N3—Bi2—O8ⁱⁱ	62.62 (8)	C23—C24—C25	118.5 (3)
O1—Bi2—O8ⁱⁱ	133.56 (8)	C23—C24—H24A	120.8
O15—Bi2—O8ⁱⁱ	85.53 (7)	C25—C24—H24A	120.8
O9—Bi2—O8ⁱⁱ	86.61 (7)	C26—C25—C24	119.0 (3)
O13—Bi2—O1W	139.60 (8)	C26—C25—H25A	120.5
O11—Bi2—O1W	129.27 (8)	C24—C25—H25A	120.5
N4—Bi2—O1W	125.24 (8)	C27—C26—C25	118.7 (3)
N3—Bi2—O1W	113.37 (8)	C27—C26—H26A	120.7
O1—Bi2—O1W	70.76 (8)	C25—C26—H26A	120.7
O15—Bi2—O1W	70.62 (7)	N4—C27—C26	121.7 (3)
O9—Bi2—O1W	75.85 (7)	N4—C27—C28	115.2 (3)
O8ⁱⁱ—Bi2—O1W	64.79 (7)	C26—C27—C28	123.1 (3)
C1—O1—Bi2	127.3 (2)	O16—C28—O15	125.9 (3)
C1—O1—Bi1	121.4 (2)	O16—C28—C27	117.2 (3)
Bi2—O1—Bi1	110.39 (9)	O15—C28—C27	116.9 (3)
C7—O3—Bi1	124.1 (2)	C30—N5—C29	111.4 (3)
C8—O5—Bi1	118.5 (2)	C30—N5—H5N1	106.3
C14—O7—Bi1	122.1 (2)	C29—N5—H5N1	110.5
C14—O8—Bi2ⁱⁱ	140.2 (2)	C30—N5—H5N2	111.7
C15—O9—Bi1	122.0 (2)	C29—N5—H5N2	111.4
C15—O9—Bi2	120.3 (2)	H5N1—N5—H5N2	105.1
Bi1—O9—Bi2	108.23 (9)	N5—C29—C30ⁱⁱⁱ	110.0 (3)
C21—O11—Bi2	123.5 (2)	N5—C29—H29A	109.7
C22—O13—Bi2	122.5 (2)	C30ⁱⁱⁱ—C29—H29A	109.7
C22—O14—Bi1ⁱ	147.0 (2)	N5—C29—H29B	109.7
C28—O15—Bi2	119.9 (2)	C30ⁱⁱⁱ—C29—H29B	109.7
C6—N1—C2	120.1 (3)	H29A—C29—H29B	108.2
C6—N1—Bi1	117.1 (2)	N5—C30—C29ⁱⁱⁱ	109.5 (3)
C2—N1—Bi1	122.8 (2)	N5—C30—H30A	109.8
C13—N2—C9	120.1 (3)	C29ⁱⁱⁱ—C30—H30A	109.8
C13—N2—Bi1	116.9 (2)	N5—C30—H30B	109.8
C9—N2—Bi1	122.7 (2)	C29ⁱⁱⁱ—C30—H30B	109.8
C20—N3—C16	119.7 (3)	H30A—C30—H30B	108.2
C20—N3—Bi2	116.9 (2)	C32—N6—C31	110.7 (3)
C16—N3—Bi2	122.9 (2)	C32—N6—H6N1	116.6
C27—N4—C23	120.3 (3)	C31—N6—H6N1	105.6
C27—N4—Bi2	121.4 (2)	C32—N6—H6N2	111.5
C23—N4—Bi2	117.3 (2)	C31—N6—H6N2	114.5
O2—C1—O1	126.6 (3)	H6N1—N6—H6N2	97.4
O2—C1—C2	118.3 (3)	N6—C31—C32^iv	109.6 (3)
O1—C1—C2	115.1 (3)	N6—C31—H31A	109.7
N1—C2—C3	121.2 (3)	C32^iv—C31—H31A	109.8
N1—C2—C1	116.5 (3)	N6—C31—H31B	109.7
C3—C2—C1	122.3 (3)	C32^iv—C31—H31B	109.7
C4—C3—C2	119.3 (3)	H31A—C31—H31B	108.2
C4—C3—H3A	120.4	N6—C32—C31^iv	110.3 (3)
C2—C3—H3A	120.4	N6—C32—H32A	109.6
C3—C4—C5	119.5 (3)	C31^iv—C32—H32A	109.6
C3—C4—H4A	120.3	N6—C32—H32B	109.6
C5—C4—H4A	120.3	C31^iv—C32—H32B	109.6
C6—C5—C4	117.8 (3)	H32A—C32—H32B	108.1
C6—C5—H5A	121.1	Bi2—O1W—H1W1	99.6
C4—C5—H5A	121.1	Bi2—O1W—H1W2	130.1
N1—C6—C5	122.2 (3)	H1W1—O1W—H1W2	106.1
N1—C6—C7	115.4 (3)	H2W1—O2W—H2W2	119.0

O13—Bi2—O1—C1	124.0 (3)	O13—Bi2—N3—C16	79.3 (3)
O11—Bi2—O1—C1	61.7 (3)	O11—Bi2—N3—C16	177.7 (3)
N4—Bi2—O1—C1	54.7 (3)	N4—Bi2—N3—C16	128.7 (2)
N3—Bi2—O1—C1	176.7 (3)	O1—Bi2—N3—C16	25.6 (3)
O15—Bi2—O1—C1	−9.8 (3)	O15—Bi2—N3—C16	−144.6 (2)
O9—Bi2—O1—C1	−159.9 (3)	O9—Bi2—N3—C16	1.0 (2)
O8ⁱⁱ—Bi2—O1—C1	−95.7 (3)	O8ⁱⁱ—Bi2—N3—C16	−99.7 (3)
O1W—Bi2—O1—C1	−78.4 (3)	O1W—Bi2—N3—C16	−58.0 (3)
O13—Bi2—O1—Bi1	−67.02 (10)	O13—Bi2—N4—C27	179.2 (3)
O11—Bi2—O1—Bi1	−129.36 (14)	O11—Bi2—N4—C27	80.9 (3)
N4—Bi2—O1—Bi1	−136.30 (11)	N3—Bi2—N4—C27	127.4 (2)
N3—Bi2—O1—Bi1	−14.30 (15)	O1—Bi2—N4—C27	−102.5 (3)
O15—Bi2—O1—Bi1	159.20 (10)	O15—Bi2—N4—C27	−5.4 (2)
O9—Bi2—O1—Bi1	9.11 (8)	O9—Bi2—N4—C27	−150.8 (2)
O8ⁱⁱ—Bi2—O1—Bi1	73.28 (12)	O8ⁱⁱ—Bi2—N4—C27	45.2 (3)
O1W—Bi2—O1—Bi1	90.61 (10)	O1W—Bi2—N4—C27	−44.9 (3)
O7—Bi1—O1—C1	79.5 (3)	O13—Bi2—N4—C23	10.5 (2)
O3—Bi1—O1—C1	3.8 (3)	O11—Bi2—N4—C23	−87.8 (2)
N2—Bi1—O1—C1	110.5 (3)	N3—Bi2—N4—C23	−41.3 (3)
N1—Bi1—O1—C1	−1.5 (2)	O1—Bi2—N4—C23	88.7 (2)
O9—Bi1—O1—C1	160.3 (3)	O15—Bi2—N4—C23	−174.1 (3)
O5—Bi1—O1—C1	−140.2 (2)	O9—Bi2—N4—C23	40.4 (3)
O14ⁱ—Bi1—O1—C1	−67.0 (3)	O8ⁱⁱ—Bi2—N4—C23	−123.5 (2)
O7—Bi1—O1—Bi2	−90.28 (10)	O1W—Bi2—N4—C23	146.3 (2)
O3—Bi1—O1—Bi2	−165.93 (9)	Bi2—O1—C1—O2	−6.5 (5)
N2—Bi1—O1—Bi2	−59.29 (15)	Bi1—O1—C1—O2	−174.4 (3)
N1—Bi1—O1—Bi2	−171.27 (13)	Bi2—O1—C1—C2	172.4 (2)
O9—Bi1—O1—Bi2	−9.44 (9)	Bi1—O1—C1—C2	4.5 (4)
O5—Bi1—O1—Bi2	50.04 (16)	C6—N1—C2—C3	1.8 (5)
O14ⁱ—Bi1—O1—Bi2	123.22 (9)	Bi1—N1—C2—C3	−174.4 (2)
O7—Bi1—O3—C7	−79.5 (3)	C6—N1—C2—C1	−178.4 (3)
N2—Bi1—O3—C7	−146.9 (3)	Bi1—N1—C2—C1	5.3 (4)
N1—Bi1—O3—C7	−7.2 (2)	O2—C1—C2—N1	172.7 (3)
O9—Bi1—O3—C7	−142.5 (2)	O1—C1—C2—N1	−6.3 (5)
O5—Bi1—O3—C7	146.4 (3)	O2—C1—C2—C3	−7.6 (5)
O1—Bi1—O3—C7	−12.4 (3)	O1—C1—C2—C3	173.5 (3)
O14ⁱ—Bi1—O3—C7	65.0 (3)	N1—C2—C3—C4	−0.7 (5)
O7—Bi1—O5—C8	−18.4 (3)	C1—C2—C3—C4	179.5 (3)
O3—Bi1—O5—C8	65.2 (2)	C2—C3—C4—C5	−1.0 (5)
N2—Bi1—O5—C8	−8.7 (2)	C3—C4—C5—C6	1.7 (5)
N1—Bi1—O5—C8	104.1 (3)	C2—N1—C6—C5	−1.1 (5)
O9—Bi1—O5—C8	−87.2 (2)	Bi1—N1—C6—C5	175.4 (3)
O1—Bi1—O5—C8	−141.3 (2)	C2—N1—C6—C7	179.3 (3)
O14ⁱ—Bi1—O5—C8	141.9 (3)	Bi1—N1—C6—C7	−4.3 (4)
O3—Bi1—O7—C14	−73.4 (2)	C4—C5—C6—N1	−0.7 (5)
N2—Bi1—O7—C14	−3.8 (2)	C4—C5—C6—C7	178.9 (3)
N1—Bi1—O7—C14	−139.5 (3)	Bi1—O3—C7—O4	−172.1 (3)
O9—Bi1—O7—C14	79.8 (2)	Bi1—O3—C7—C6	7.7 (4)
O5—Bi1—O7—C14	5.6 (3)	N1—C6—C7—O4	178.1 (3)
O1—Bi1—O7—C14	153.2 (3)	C5—C6—C7—O4	−1.5 (5)
O14ⁱ—Bi1—O7—C14	−141.3 (2)	N1—C6—C7—O3	−1.6 (4)
O7—Bi1—O9—C15	−129.3 (3)	C5—C6—C7—O3	178.7 (3)
O3—Bi1—O9—C15	−62.6 (3)	Bi1—O5—C8—O6	−174.0 (3)
N2—Bi1—O9—C15	−58.3 (3)	Bi1—O5—C8—C9	6.9 (4)
N1—Bi1—O9—C15	176.9 (2)	C13—N2—C9—C10	−2.6 (5)
O5—Bi1—O9—C15	6.6 (3)	Bi1—N2—C9—C10	170.4 (2)
O1—Bi1—O9—C15	155.1 (3)	C13—N2—C9—C8	176.3 (3)
O14ⁱ—Bi1—O9—C15	81.9 (3)	Bi1—N2—C9—C8	−10.7 (4)
O7—Bi1—O9—Bi2	84.45 (9)	O6—C8—C9—N2	−177.4 (3)
O3—Bi1—O9—Bi2	151.22 (13)	O5—C8—C9—N2	1.8 (4)
N2—Bi1—O9—Bi2	155.47 (11)	O6—C8—C9—C10	1.5 (5)
N1—Bi1—O9—Bi2	30.64 (15)	O5—C8—C9—C10	−179.3 (3)
O5—Bi1—O9—Bi2	−139.62 (9)	N2—C9—C10—C11	0.5 (5)
O1—Bi1—O9—Bi2	8.88 (8)	C8—C9—C10—C11	−178.2 (3)
O14ⁱ—Bi1—O9—Bi2	−64.28 (12)	C9—C10—C11—C12	1.6 (5)
O13—Bi2—O9—C15	−75.6 (2)	C10—C11—C12—C13	−1.7 (5)
O11—Bi2—O9—C15	−0.1 (3)	C9—N2—C13—C12	2.5 (5)
N4—Bi2—O9—C15	−104.6 (3)	Bi1—N2—C13—C12	−170.9 (3)
N3—Bi2—O9—C15	3.8 (2)	C9—N2—C13—C14	−176.1 (3)
O1—Bi2—O9—C15	−156.1 (3)	Bi1—N2—C13—C14	10.5 (4)
O15—Bi2—O9—C15	141.7 (2)	C11—C12—C13—N2	−0.3 (5)
O8ⁱⁱ—Bi2—O9—C15	64.7 (2)	C11—C12—C13—C14	178.2 (3)
O1W—Bi2—O9—C15	129.5 (3)	Bi2ⁱⁱ—O8—C14—O7	128.7 (3)
O13—Bi2—O9—Bi1	71.32 (10)	Bi2ⁱⁱ—O8—C14—C13	−51.2 (5)
O11—Bi2—O9—Bi1	146.80 (9)	Bi1—O7—C14—O8	−169.4 (2)
N4—Bi2—O9—Bi1	42.35 (15)	Bi1—O7—C14—C13	10.5 (4)
N3—Bi2—O9—Bi1	150.68 (12)	N2—C13—C14—O8	166.2 (3)
O1—Bi2—O9—Bi1	−9.18 (8)	C12—C13—C14—O8	−12.4 (5)
O15—Bi2—O9—Bi1	−71.42 (16)	N2—C13—C14—O7	−13.7 (4)
O8ⁱⁱ—Bi2—O9—Bi1	−148.38 (9)	C12—C13—C14—O7	167.7 (3)
O1W—Bi2—O9—Bi1	−83.55 (9)	Bi1—O9—C15—O10	32.0 (5)
O13—Bi2—O11—C21	83.7 (3)	Bi2—O9—C15—O10	174.4 (3)
N4—Bi2—O11—C21	149.8 (3)	Bi1—O9—C15—C16	−149.7 (2)
N3—Bi2—O11—C21	12.7 (2)	Bi2—O9—C15—C16	−7.4 (4)
O1—Bi2—O11—C21	142.7 (2)	C20—N3—C16—C17	1.3 (5)
O15—Bi2—O11—C21	−142.8 (3)	Bi2—N3—C16—C17	173.0 (3)
O9—Bi2—O11—C21	16.4 (3)	C20—N3—C16—C15	−176.7 (3)
O8ⁱⁱ—Bi2—O11—C21	−54.3 (2)	Bi2—N3—C16—C15	−4.9 (4)
O1W—Bi2—O11—C21	−88.9 (3)	O10—C15—C16—N3	−173.6 (3)
O11—Bi2—O13—C22	67.3 (3)	O9—C15—C16—N3	8.1 (5)
N4—Bi2—O13—C22	−3.0 (2)	O10—C15—C16—C17	8.5 (5)
N3—Bi2—O13—C22	132.2 (3)	O9—C15—C16—C17	−169.9 (3)
O1—Bi2—O13—C22	−87.9 (3)	N3—C16—C17—C18	−2.6 (5)
O15—Bi2—O13—C22	−8.7 (3)	C15—C16—C17—C18	175.3 (3)
O9—Bi2—O13—C22	−161.0 (3)	C16—C17—C18—C19	1.9 (5)
O8ⁱⁱ—Bi2—O13—C22	133.4 (2)	C17—C18—C19—C20	−0.1 (5)
O1W—Bi2—O13—C22	−121.6 (3)	C16—N3—C20—C19	0.7 (5)
O13—Bi2—O15—C28	3.6 (3)	Bi2—N3—C20—C19	−171.5 (3)
O11—Bi2—O15—C28	−77.2 (2)	C16—N3—C20—C21	−179.6 (3)
N4—Bi2—O15—C28	−2.2 (2)	Bi2—N3—C20—C21	8.1 (4)
N3—Bi2—O15—C28	−111.9 (3)	C18—C19—C20—N3	−1.3 (5)
O1—Bi2—O15—C28	75.6 (2)	C18—C19—C20—C21	179.1 (3)
O9—Bi2—O15—C28	131.8 (2)	Bi2—O11—C21—O12	167.7 (3)
O8ⁱⁱ—Bi2—O15—C28	−150.9 (2)	Bi2—O11—C21—C20	−13.3 (4)
O1W—Bi2—O15—C28	144.3 (3)	N3—C20—C21—O12	−178.5 (3)
O7—Bi1—N1—C6	104.3 (3)	C19—C20—C21—O12	1.1 (5)
O3—Bi1—N1—C6	5.7 (2)	N3—C20—C21—O11	2.4 (4)
N2—Bi1—N1—C6	53.0 (3)	C19—C20—C21—O11	−177.9 (3)
O9—Bi1—N1—C6	158.5 (2)	Bi1ⁱ—O14—C22—O13	−149.2 (3)
O5—Bi1—N1—C6	−36.5 (3)	Bi1ⁱ—O14—C22—C23	31.2 (6)
O1—Bi1—N1—C6	−178.6 (3)	Bi2—O13—C22—O14	176.5 (3)
O14ⁱ—Bi1—N1—C6	−76.9 (2)	Bi2—O13—C22—C23	−3.9 (4)
O7—Bi1—N1—C2	−79.4 (3)	C27—N4—C23—C24	−4.3 (5)
O3—Bi1—N1—C2	−178.0 (3)	Bi2—N4—C23—C24	164.6 (3)
N2—Bi1—N1—C2	−130.7 (2)	C27—N4—C23—C22	175.3 (3)
O9—Bi1—N1—C2	−25.1 (3)	Bi2—N4—C23—C22	−15.9 (4)
O5—Bi1—N1—C2	139.9 (2)	O14—C22—C23—N4	−167.1 (3)
O1—Bi1—N1—C2	−2.3 (2)	O13—C22—C23—N4	13.3 (4)
O14ⁱ—Bi1—N1—C2	99.4 (3)	O14—C22—C23—C24	12.5 (5)
O7—Bi1—N2—C13	−4.3 (2)	O13—C22—C23—C24	−167.2 (3)
O3—Bi1—N2—C13	94.9 (2)	N4—C23—C24—C25	4.0 (5)
N1—Bi1—N2—C13	49.2 (3)	C22—C23—C24—C25	−175.5 (3)
O9—Bi1—N2—C13	−82.9 (2)	C23—C24—C25—C26	−0.6 (5)
O5—Bi1—N2—C13	−176.8 (3)	C24—C25—C26—C27	−2.4 (5)
O1—Bi1—N2—C13	−35.8 (3)	C23—N4—C27—C26	1.1 (5)
O14ⁱ—Bi1—N2—C13	140.6 (2)	Bi2—N4—C27—C26	−167.3 (3)
O7—Bi1—N2—C9	−177.5 (3)	C23—N4—C27—C28	179.7 (3)
O3—Bi1—N2—C9	−78.3 (2)	Bi2—N4—C27—C28	11.3 (4)
N1—Bi1—N2—C9	−124.0 (2)	C25—C26—C27—N4	2.3 (5)
O9—Bi1—N2—C9	103.9 (3)	C25—C26—C27—C28	−176.2 (3)
O5—Bi1—N2—C9	10.0 (2)	Bi2—O15—C28—O16	−172.0 (3)
O1—Bi1—N2—C9	150.9 (2)	Bi2—O15—C28—C27	8.5 (4)
O14ⁱ—Bi1—N2—C9	−32.6 (3)	N4—C27—C28—O16	167.6 (3)
O13—Bi2—N3—C20	−108.7 (3)	C26—C27—C28—O16	−13.8 (5)
O11—Bi2—N3—C20	−10.3 (2)	N4—C27—C28—O15	−12.9 (4)
N4—Bi2—N3—C20	−59.3 (3)	C26—C27—C28—O15	165.7 (3)
O1—Bi2—N3—C20	−162.4 (2)	C30—N5—C29—C30ⁱⁱⁱ	−58.4 (4)
O15—Bi2—N3—C20	27.4 (3)	C29—N5—C30—C29ⁱⁱⁱ	58.0 (4)
O9—Bi2—N3—C20	172.9 (3)	C32—N6—C31—C32^iv	−58.1 (4)
O8ⁱⁱ—Bi2—N3—C20	72.2 (2)	C31—N6—C32—C31^iv	58.5 (4)
O1W—Bi2—N3—C20	114.0 (2)

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x, −y+1, −z; (iii) −x, −y+2, −z+1; (iv) −x−2, −y, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5N1···O2Wⁱⁱⁱ	0.90	2.00	2.761 (4)	141
N5—H5N2···O6	0.90	1.86	2.722 (4)	160
N6—H6N1···O16^v	0.90	1.78	2.676 (4)	176
N6—H6N2···O12	0.90	1.95	2.762 (4)	149
O1W—H1W1···O7	0.85	2.08	2.891 (3)	160
O1W—H1W2···O9ⁱⁱ	0.85	2.53	3.337 (4)	158
O2W—H2W1···O14	0.85	2.04	2.887 (4)	176
O2W—H2W2···O5	0.85	2.35	3.162 (4)	159

Symmetry codes: (ii) −x, −y+1, −z; (iii) −x, −y+2, −z+1; (v) −x−1, −y, −z.

Experimental details

Crystal data
Chemical formula	(C₄H₁₂N₂)[Bi₂(C₇H₃NO₄)₄(H₂O)]·H₂O
M_r	1202.56
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	10.8111 (4), 12.1660 (5), 14.0402 (5)
α, β, γ (°)	96.094 (1), 93.169 (1), 113.848 (1)
V (Å³)	1669.65 (11)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	10.62
Crystal size (mm)	0.15 × 0.15 × 0.10

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.204, 0.346
No. of measured, independent and observed [I > 2σ(I)] reflections	22723, 8005, 6952
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.022, 0.048, 1.03
No. of reflections	8005
No. of parameters	523
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.32, −0.82

Computer programs: APEX2 (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5N1···O2Wⁱ	0.90	2.00	2.761 (4)	141
N5—H5N2···O6	0.90	1.86	2.722 (4)	160
N6—H6N1···O16ⁱⁱ	0.90	1.78	2.676 (4)	176
N6—H6N2···O12	0.90	1.95	2.762 (4)	149
O1W—H1W1···O7	0.85	2.08	2.891 (3)	160
O1W—H1W2···O9ⁱⁱⁱ	0.85	2.53	3.337 (4)	158
O2W—H2W1···O14	0.85	2.04	2.887 (4)	176
O2W—H2W2···O5	0.85	2.35	3.162 (4)	159

Symmetry codes: (i) −x, −y+2, −z+1; (ii) −x−1, −y, −z; (iii) −x, −y+1, −z.

References

Aghabozorg, H., Attar Gharamaleki, J., Ghadermazi, M., Ghasemikhah, P. & Soleimannejad, J. (2007). Acta Cryst. E63, m1803–m1804. Web of Science CSD CrossRef IUCr Journals Google Scholar
Aghabozorg, H., Attar Gharamaleki, J., Ghasemikhah, P., Ghadermazi, M. & Soleimannejad, J. (2007). Acta Cryst. E63, m1710–m1711. Web of Science CSD CrossRef IUCr Journals Google Scholar
Aghabozorg, H., Daneshvar, S., Motyeian, E., Ghadermazi, M. & Attar Gharamaleki, J. (2007). Acta Cryst. E63, m2468–m2469. Web of Science CSD CrossRef IUCr Journals Google Scholar
Aghabozorg, H., Motyeian, E., Aghajani, Z., Ghadermazi, M. & Attar Gharamaleki, J. (2007). Acta Cryst. E63, m1754–m1755. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sharif, M. A., Aghabozorg, H. & Moghimi, A. (2007). Acta Cryst. E63, m1599–m1601. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheshmani, S., Ghadermazi, M. & Aghabozorg, H. (2006). Acta Cryst. E62, o3620–o3622. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 64| Part 2| February 2008| Page m374

doi:10.1107/S160053680800161X

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Poly[piperazinediium [[aqua­bis­muth­ate(III)]-di-μ-pyridine-2,6-di­carboxyl­ato-bis­­muthate(III)-di-μ-pyridine-2,6-di­carboxyl­ato] monohydrate]

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Experimental

Crystal data

Data collection

Refinement

Supporting information

References

metal-organic compounds

Poly[piperazinediium [[aquabismuthate(III)]-di-μ-pyridine-2,6-dicarboxylato-bismuthate(III)-di-μ-pyridine-2,6-dicarboxylato] monohydrate]